I set up an IPSec tunnel between my home network and work. We have a Sharepoint server in the office that I used to be able to access just fine remotely. Now that requests to the server are routed through the tunnel, I can browse the share in Windows Explorer, and copy files to a local folder. When I try to open a Word document directly from Sharepoint, however, MS Word will hang. I can open it in WordPad, but I get a security warning (despite the fact that I added the server to my local network in the IE Internet settings).

This doesn't sound like an IPSec issue - have you run Fiddler on the problem computer and captured the web traffic? My guess is that there is a DNS or other misconfiguration that is causing MS Word to hang.
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GoyuixFeb 7 '12 at 3:18

1 Answer
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I suspect this has more to do with Sharepoint than anything else, and I'm not familiar enough with it in this regard to offer suggestions specific to it. For VPNs in general and pfSense, make sure you're on 2.0 release or newer, which include MSS clamping by default to 1400 on VPN traffic. Generally hit and miss connectivity problems (if that's what it is) are because of large packets getting dropped. I suspect that's not likely the case though since it opens in WordPad but not Word, the network and firewall have no idea what application you're opening files in and would be impacted in the same way if it were the cause.

So far nothing points to Sharepoint. I think this only affects certain documents, and it might be the Windows Attachment Manager (support.microsoft.com/kb/883260). I am still researching (whenever there is time).
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cdonnerFeb 9 '12 at 4:02